If the Second City calls you away from the Big Apple, Southwest Airlines® has you covered with cheap, nonstop flights. Southwest® is proud to offer flights from New York (LaGuardia) to Chicago (Midway) at prices that'll melt a hardened New Yorker heart with their Midwestern nice. Booking is straightforward, no matter if you're traveling for fun, family, business, or something else. Have flexible dates? Search for your New York (LaGuardia) to Chicago (Midway) flight on our Low Fare Calendar and find our cheapest prices within your timetable. Check out Southwest Vacations® and build yourself a package deal with flights, hotels, rental cars, and more to make the most of our low prices.
Explore New York (LaGuardia) to Chicago (Midway) flights and book your next trip to Chi-Town now!
New York (LaGuardia), NY to Chicago (Midway), IL
departing on 11/04
one-way starting at*$45
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 58 travel days available.
Middle seats open through November 30
Full exchange of fresh, outdoor air every 2-3 minutes while inflight
Face coverings required
Average flight time: 2 hours 35 minutes
Departing from: LaGuardia Airport (LGA)
Arriving at: Chicago Midway International Airport (MDW)
Nonstop flightsper day
Other popular flights from New YorkView our interactive map
†Based on DOT published scheduled average flights Monday-Friday between 8/20/2020 and 4/11/2021, as of 8/20/2020.
There's no chip on the City of the Big Shoulders about folks thinking they're lesser than New York City. That's like comparing the Big Apple to oranges, frankly. The Second City is second to none when it comes to pizza, improv, cursed baseball teams, fires started by cows, and so much more. The skyline boasts the tallest building in the Western hemisphere—NYC doesn't have that. New York City has Broadway; Chicago has Broadway in Chicago, where Broadway comes to visit. Chicago also happens to be the market where stage shows test before heading to the East Coast. One might say, if you can make it in Chicago, you can really make it anywhere.
Faux competition aside, New Yorkers can find a lot to love in Chicago. Freshwater abounds thanks to the shores of Lake Michigan; take a dip if your visit is during the summer, or consider joining a Polar Plunge if you're around during the arctic depths of a Midwestern winter. New Yorkers are no strangers to public transit, and so will likely take to the CTA like ducks to water. When deplaning at Midway, it's just a half hour Orange Line elevated train ride to the Loop—Chicago's downtown. From there, the city is at your feet thanks to the train and bus system. And like NYC, Chicago is on a grid system—getting lost? Fuggetaboutit.
When you fly from New York (LaGuardia) to Chicago (Midway), you can put the money you save on your nonstop flight toward enjoying the Windy City. Take a Chicago River boat ride, an architectural walking tour, or sit down for a Michelin-starred meal. Maximize your savings by exploring our deals on rental cars, hotels, and more. We even have whole vacation packages if you'd like to round out your trip while protecting your wallet. Whether you're in Chicago just briefly or for an extended period of time, your trip will go smoothly with Southwest.
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
At Southwest, we know that a memorable trip from New York City to Chicago is made of more than a cheap nonstop flight from LaGuardia to Midway. That's why we offer more, from booking to boarding. Find out more about the Southwest Travel Experience while you book your New York (LaGuardia) to Chicago (Midway) flight.
Whether you're visiting Chicago for several days or just stopping by on the way to somewhere else, traveling with Southwest is always straightforward. No hidden fees and low fares—that's our Transfarency® promise. Stay up to date with our latest flight deals: Enroll in our Click 'N Save® emails. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.